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rinhaler · 1 year ago

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Rin Itoshi and female s/o taking each other first time

omgggggg i tried to make it romantic and sweet but i do love a slutty ass dude who's in control so apologies if this isnt exactly what u wanted hehe

warnings: 18+ MDNI, fem!reader, virgin!rin, virgin!reader, fingering, best friends to lovers, mutual pining, tit sucking, "just the tip" pfft, slight manipulation, brief condom use, premature ejaculation, creampie.

words: 2.9k

Your heart races as you watch Rin scroll through his phone and find some music to play. He looks so serious, though that’s nothing new. You don’t dare speak, worried you’ll say the wrong thing if you do. He looks up at you, briefly, offering a weak smile before looking through his phone again.

“We don’t have to do this, you know.” he tells you without even looking at you. You watch him as he starts hooking up his phone to the Bluetooth speaker in your room, and you shuffle uncomfortably on top of your bed.

“I want to… ‘m just scared.” you confess, breath shaking slightly as you exhale. “Do you still want to?” you wonder, feeling shy as you ask. You’re sure he wouldn’t be here if he didn’t want to, though.

Rin doesn’t do anything he has no interest in.

“Yeah.” he tells you, setting his phone down before looking back at you, finally. He’s so far away, it feels too formal. Though you assume he wants to set the pace and make sure everything is comfortable for you both before you proceed. “We agreed,”

“I know.” you nod, recalling the moment you decided as teenagers to give each other your virginities if you hadn’t lost them after you turned twenty. “Just checking.”

The concept of Rin being single, let alone a virgin, is something you can’t even begin to comprehend. You’ve been best friends with him since you could talk. You remember him having no interest in you until you forced your way into playing soccer games with him and his brother. You soon gave it up once you got what you wanted, but you’ve been inseparable ever since.

Girls have always thrown themselves at Rin, but he never cared. Not really. You remember him having one girlfriend and it never went anywhere. It only lasted three weeks. He told you the gory details of their sex lives, though. Only because you asked.

It didn’t go past hand stuff.

“I brought condoms.” he tells you, pulling a box from his bag and setting them down on the desk he’s sitting by.

“I- I’m on the pill.” you respond. “I heard it feels better without… those. But we should use them.”

“Okay, yeah.” he agrees.

“… but we don’t have to.”

“I’ll use one.” he assures you, not wanting to make you feel pressured to go raw for his benefit. Though you’re sure it would be for yours, too. “If you want me to take it off, I can do that.”

You nod, agreeing.

“This is so…” you think, searching around the room for any inspiration of a descriptor to use. He stares at you, intently, wondering what you might say. He’d never tell you, but he’s just as nervous as you are. Of course he has an edge of experience ahead of you, but he’s still clueless. He wants to make sure this is going to be nice for you.

Perfect, if possible.

“What?”

“Formal.” you shrug.

“Oh, I’m sorry.” he responds, scratching his neck as he thinks about what you told him. He looks around, feeling a little too awkward to make eye contact. “I just want to make sure everything’s going to be okay…”

“It’s fine, you’re right.” you smile, “I just thought my first time would be… romantic. It’s stupid, I’m sorry.” you shake your head, dismissing the idea.

You knew you’d end up here with him eventually. You had no intention of losing your virginity to anyone else, after all. You’ve been in love with him for years, and finding out he got a girlfriend almost killed you. It was hard hearing about how they became intimate, but you were so fucking relieved when they broke up.

He only decided to get a girlfriend because he thought you weren’t interested in him, though. You’ve always been a forbidden fruit he wouldn’t dare try to cross a line with. You’re his best friend, after all. He wouldn’t want the romantic feelings he has towards you to ruin that.

“It’s not stupid.” he assures you. “Here, pick some music.” he hands you his phone.

You start to scroll and realise you’re looking on a playlist he created aptly named sex playlist. It makes you giggle, but you don’t comment. And you don’t pay him any mind as he leaves the room while you continue searching for a song.

The boy has good taste, you soon realise.

He comes back a few minutes later with some candles from a nearby cupboard. He knows you too well. You hoard them, you always have. You get an abundance each year for Christmas and rarely use them. He starts lighting them and placing them around the room.

You finally look up as he turns the light on, the room dimly lit by the burning flames scattered around.

“Is this better? I should have gotten some rose petals or something…”

“N-No, this is fine.” you smile, “Thank you, Rinnie, this is nice.”

He clears his throat and sits beside you on your bed. You quickly hand him his phone, prompting him to lean over to place it back down on your desk.

Your heartbeat begins to increase rapidly as he faces you. You haven’t even so much as kissed before, let alone what else will follow. He reaches out to caress your face, and it takes all of your willpower to not flinch.

“R-Rin… do you, um, d-do you watch…”

“Porn? Yeah. Do you?”

His reply makes your face flush with heat and the thought of confessing your own truth makes you even hotter. You look away from him, twiddling your fingers in your lap and looking at those instead.

“I know it won’t be like that… it’s your first time. And mine.” he reminds you.

He’s always been so mature. And you’re glad he’s doing all he can to put you at ease. He puts a finger under your chin, forcing you to look up at him again. You gulp, nervously, before nodding. He smirks at that.

“Good, I’m glad,” he tells you, beautiful jade eyes flickering with flames as he stares at you. “Means you know what you like.” he leans into you, an attempt to kiss which you immediately back away from. And you apologise, profusely, assuring him that you’re still a little nervous.

“I— I know guys can, you know, it can be quick… s-so don’t feel bad.”

“Don’t worry about that.” he shakes his head. “If I cum quickly, I’ll make sure you finish.”

He closes the distance between the two of you, his lips planting softly on your own. His eyes close as he loses himself to it, though you keep yours open for a little while as you process what is happening.

You’re making out with your best friend!

Though when his large, dominating hands begin to fondle your chest, you pull away entirely.

“Sorry, did I hurt you?” he wonders.

“N-No, I didn’t expect you to be so confident.” you whisper, and he kisses you again, smiling into it.

Your eyes close as you allow him to continue locking lips with you. His hand entirely gropes one of your tits and his thumb casually strokes over it. Even through the layers of your crop top and bra, you find yourself mewling softly.

He smooths his hand over the curve of your waist until he reaches the bottom of your crop top. His fingers breach upwards towards your bra, roughly groping at it and the fat of your tits.

“O-Ow.” you speak, softly.

“Sorry,” he whispers back, “Can I take your top off?” he asks between continuous kisses.

“Uh-huh.” you nod, dumbly.

He breaks the kiss to quickly pull your crop top over your head. His lips attach to yours again almost instantly as he starts to fiddle with your bra. He stops kissing you, again, to look over your shoulder so that he can undo the clasp. You gasp when he finally unhooks it, keeping the pink material against your chest to preserve your modesty.

“Can I see?” he asks, his eyes moving between yours and your hands. You hum, nervously, but nod. He helps you pull down your straps as you keep the material held firmly against your chest. Sighing, slightly panic in your voice as you strip the material away. “Fuuuuck…” he mutters to himself, adjusting his hardening cock in his pants as he looks at you.

“You should take something off.” you suggest before he can kiss you again. He immediately pulls his t-shirt over his head, tousling his hair back into place right after.

You continue to moan against his lips when he kisses you again. And they only get louder as he kisses down your neck whilst flicking his thumb over your pebbled nipple. He grunts against your skin, battling on whether he should say something to you or stay silent.

He’d hate to ruin the mood.

“Are you hard yet?” you ask him, your shy demeanour leaving you as you lose yourself to the sensation of his hands caressing your body. “S-Should we do it?”

“Wanna feel?” he asks, not waiting for an answer as he pulls your hand towards the bulge in his jeans, moaning immediately from the contact. “Look what you’ve done to me.” he laughs, pulling you closer and hooking one of your legs over his own.

He scratches the back of his nails up your thigh, stopping just short of dipping under your skirt as you shiver from the touch. His eyes find yours, kissing you reassuringly.

“Can I feel you?” he wonders, and, of course, you nod. His fingers disappear under your pleated skirt, quickly cupping your panty-clad mound. He barely gasps when he comes into contact with your panties. “You’re so wet…”

“S-Stop…” you reply, shyly, “s’embarrassing…” you tell him.

“You need to be wet for me,” he responds, that big, logical, brain of his immediately putting you in your place. Reminding you that he is the one with a little more experience and you need to listen to him. “You’ll be so tight… even for a finger.”

He forces your body down, flat against the bed and flips up your skirt. The cute triangular shape of your panties makes his cock throb, and he moves them into the crease of your thigh.

“Tell me if it hurts…” he requests, staring into your eyes as deft fingers come into contact with sopping flesh. He runs them through your folds, and you jolt when a finger tip grazes your clit. He moves it towards your hole, slowly teasing around it before pushing in. He stops, quickly, when you yelp. “Sorry, I’ll go slower. Hold onto me.” he instructs, a hand wraps around his bicep and squeezes as he continues to plunge his longer finger deep inside.

“Kiss me,” you whimper, pathetically. He drops his head so that your lips can meet again. He devours the moans and cries you emit as he curls his finger in and out of you. It feels odd, but not unpleasant. It’s still painful but it begins to subside.

“Gonna add another, okay?” he asks, and you nod. You hiss, instantly, hands flying down to pull his away. “Sh, sh sh, I’ll go slow again, okay? Gotta be able to take them or we can’t fuck.”

You fight back tears as the stretch begins to sting. He sinks his head lower, taking one of your hardened nipples into his mouth. Your back arches off the bed slightly, coaxing him to look up at you. And then he remembers all of articles he’s read. All of the research he’s done.

He even thinks about his teammates talking about sex.

“You have to worship the clit.” he recalls one of them saying.

He pulls away from your tit, briefly, to line his thumb up with your clit and apply pressure. He circles it carefully, monitoring your expressions as he does. You yelp, trying to close your legs, but he opens them back up with his free hand.

“Are you gonna cum?” he wonders.

“It’s too much, Rinnie!” you gasp, skin tightening over your knuckles until they turn white as you grip the sheets. “S-Slow down, please! S’too much!” you cry, unable to hold back your tears any longer.

He doesn’t relent, however. Hoping the way your body trembles means you’re about to cream all over his fingers. It was an achievement he never reached with his ex without her assistance. She showed him how and where to touch to make her cum. But you’re not her. You’re perfect.

You gasp, breathlessly, as your pussy begins to tighten around his fingers. Your clit throbs as he teases it just right and you begin to cum hard and fast for him. He kisses between the valley of your breaths, whispering sweet nothings as you reach your peak and plummet back down to earth. He slows down his ministrations as you begin to shudder and twitch from the after shocks, looking up at you adoringly when you start to calm down.

“Good?” he asks.

“Very,” you pant, laughing lightly as you find your sense again. “Rinnie…” you speak, your confident bravado disappearing again as you feel naked and exposed.

“Yeah?”

“Promise me… promise you’re a virgin, too…” you say, looking up at the ceiling. You feel too needy and desperate as you speak. But that was too good for him to not know what’s he’s doing. He’s seriously only done that once on another girl? It’s a little hard to believe.

“I promise. Was it really that good?” he smirks. He kisses both of your nipples softly before sucking his fingers clean of your juices. “I’ve been preparing… reading about stuff. Asking advice. I’ve told you everything I’ve done, I swear.”

He stands up, unbuttoning his jeans and kicking off his shoes at the same time. He pulls of his jeans and underwear in the same movement, revealing his large, blushing cock.

“We don’t have to do this.” he assures you, picking up a condom from your desk and tearing the foil with his teeth. He rolls it down his length, the rubbery sheen covers the pretty pink colour of his dick. “Do you want to stop?”

“Um,” you think about it. He’s asking as if he isn’t already raring to go. You look between his erection and his intimidating stare as you think about what to say.

“What about just the tip?” he asks. And at that, you nod. He reaches under your skirt and pulls down your panties to ogle your drippy cunt one more time. He feels himself throb at the thought of splitting your virgin hole open on his fat cock. He’s always known he was big, and he really doesn’t want to hurt you. He can only hope his fingering was enough prep before you rob each other of your innocence for good.

He lines up his cockhead with your virgin slot as he cages you in beneath his wide frame. You wrap your arms around his neck and pull him down to kiss you, your moan semi silenced as he pushes his tip in.

Oh God this isn’t enough.

He knew he’d need more.

Just a little more.

He pushes in a bit further, and you pull your lips away from his to voice your concern.

“H-Hurts,” you tell him. “You’re really big.” you inflate his ego further, earning another inch of his cock.

He can’t help it, you’re spurring him on!

And he can only imagine how much better you’d feel wrapped around him without this stupid fucking rubber on. He stops pushing when you place your palms on his shoulders, forcing him to pull back a little. “Is it the condom, Rin? Is it t-too dry?” you wonder, batting your eyelashes up at him so innocently.

“Yes.” he replies, without hesitation. “I’ll take it off.”

He pulls out of you instantly. He hisses a little as he pulls at the condom too hard and it snaps back. He decides to push it up from the base of his cock, lining up with your cunt again right after.

And it’s like you’re made for him as he pushes in. He smothers any whimper you can make with a searing kiss. You feel his tongue slip into your mouth as he pushes in further and further until there’s nothing left to give.

You’re crying, again, not expecting to feel so much so soon.

“God, you’re beautiful.” he praises you. He moves his hips, slowly. His cockhead unintentionally nudges against your soft spot with every rut. The blinding pleasure prevents you from telling him, once again, that it hurts and it’s too much. “I know I said just the tip, jus’ feel so good, princess.” he whispers delicately against your skin.

And, as expected, he doesn’t last long.

A few pathetic strokes of his cock inside of you have him spilling thick spurts of white cream into your unprotected walls. He collapses on top of you, panting violently as he stuffs you full.

He was so backed up before this. He masturbates, of course, but not as much as the average guy. You’ve had this planned for a few weeks, now, so he decided to abstain so he could really enjoy feeling you for the first time.

“Fuck, ‘m sorry. Should have jerked off before I came over.”

“It’s okay.” you tell him, fingers mussing through his hair as you come to terms with the fact that you’ve finally lost your virginity, to your best friend of all people.

“I need to fuck you again,” he confesses, your fingers stop as you look down at him.

“W- now?”

“Soon,” he corrects you. “I want to taste you first.”

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